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Progress towards the total synthesis...

Fox, Richard J.

Progress towards the total synthesis of (+)-sorangicin A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Progress towards the total synthesis of (+)-sorangicin A.
Author:	Fox, Richard J.
Description:	666 p.
Notes:	Adviser: Amos B. Smith, III.
Notes:	Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3800.
Contained By:	Dissertation Abstracts International67-07B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3225459
ISBN:	9780542798948

Progress towards the total synthesis of (+)-sorangicin A.
Fox, Richard J.

Progress towards the total synthesis of (+)-sorangicin A. - 666 p.

Adviser: Amos B. Smith, III.

Thesis (Ph.D.)--University of Pennsylvania, 2006.

*Please refer to dissertation for diagrams.

ISBN: 9780542798948Subjects--Topical Terms:

193634
Chemistry, Organic.

Progress towards the total synthesis of (+)-sorangicin A.
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100 0 $a Fox, Richard J. $3 264194
245 1 0 $a Progress towards the total synthesis of (+)-sorangicin A.
300 $a 666 p.
500 $a Adviser: Amos B. Smith, III.
500 $a Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3800.
502 $a Thesis (Ph.D.)--University of Pennsylvania, 2006.
520 # $a *Please refer to dissertation for diagrams.
520 # $a Based on the lessons learned from the first generation strategy, Chapter 3 describes our improved second generation synthesis of the 2,6-dioxabicyclo[3.2.1]octane ring system. Specifically, in this revised approach, a more rapid synthesis of a modified cyclization precursor was achieved. Overall, the second generation synthesis proceeded in 17 steps and 1.7% overall yield.*
520 # $a Chapter 2 then describes the development of a first generation synthesis of the 2,6dioxabicyclo[3.2.1]octane ring system. Our strategy, based on the precedent of Mukai and Hanoaka, entailed a series of epoxide ring-openings. The first, facilitated by an TMS-alkyne Co2(CO)6 complex, proceeded in a highly regio- and stereoselective fashion. Overall, the first generation synthesis was achieved in 23 steps and 1.5% overall yield.*
520 # $a Chapter 4 then describes the stereocontrolled assembly of the C(1)-C(15) aldehyde fragment. The highlights of the synthesis included: (1) a stereoselective conjugate addition reaction to install the C(8,9) bond; (2) chemo- and stereoselective C(10) oxidation of the resulting TES-enol ether; and (3) installation of the C(11,12) olefin via reduction of the corresponding enol triflate. Overall, the synthesis of the C(1)-C(15) aldehyde fragment was achieved in 19 steps and 8% overall yield.*
520 # $a Chapter one initially discusses the isolation, structure elucidation, and biological profile of the sorangicins. Subsequently, the structure-activity relationship and chemical modification studies of (+)-sorangicin A, as well as other synthetic approaches, are presented.*
520 # $a Chapter two initially discloses the three main challenges we envisioned that our synthetic plan would address, namely: (1) the construction of the novel 2,6-dioxabicyclo[3.2.1]octane ring system through an epoxide ring-opening cascade initiated by a Co2(CO)6-alkyne complex; (2) the extension of the Petasis-Ferrier linchpin union/rearrangement tactic to aldehydes possessing alpha- and beta-oxygenation, as well as an acid sensitive acetonide group; and (3) implementation of the Kocienski-modified Julia olefination to couple highly advanced and complex fragments.
520 # $a Finally, Chapter 5 discloses our fragment coupling results, presents our model study experiments, discusses our end-game strategy, and outlines a third generation approach to the 2,6-dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A.*
520 # $a This dissertation has been divided into five chapters, and describes our synthetic efforts towards (+)-sorangicin A, a macrolide antibiotic known to inhibit RNA polymerization.
590 $a School code: 0175.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a University of Pennsylvania. $3 212781
773 0 # $g 67-07B. $t Dissertation Abstracts International
790 $a 0175
790 1 0 $a Smith, Amos B., III, $e advisor
791 $a Ph.D.
792 $a 2006
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